All The Single Ladies

Deal breakers Archives

So your boyfriend (or girlfriend) still has a profile on an online dating site...

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

I've mentioned before about all of the other writers that I adore. Well that is why I am really excited to be involved in a fun new project with a large group of them.

Allow me to introduce the folks over at Met Another Frog, Alex of the Urban Dater, Feisty Woman, KB in NYC, Lena, Lucky Girl, Man Shopper, Mike Masters, Miss Melisa Mae, Nikki B, Simone Grant, Miss Taylor Cast, and Jackie Summers, who (along with yours truly) make up the members of The Insomniac Club.

Starting today, once a month, we will take one question and each post our thoughts on the subject. The goal is to open up dialogue and maybe even inspire a good healthy debate. Plus you might even discover another blogger to enjoy.

To keep up with everything just look for the hashtag #InsomniaClub on Twitter.

And now for the first topic:

You've just discovered you partner still has an online dating profile...

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Stop making excuses

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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About a month ago I wrote a guest post on That Happened To Me about a date that I went on. As you can read in the post, the date was pretty freaking awesome and it was the first time in quite sometime that I really wanted a second date. I mean truly wanted to see the guy again. But, the second date never happened even though he pretty much planned the entire thing with me.

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Guest Post: A little something about decorum

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Today I have an awesome guest post from my dear friend Dave Sorrell, also known as @rookiephenom on Twitter. I really love guest posts from guys because sometimes (or always) it's nice to get a little perspective from them. Now, we all know that I don't think there every guy feels the exact same way about things, but still it's nice to get their perspective.  Anyway, here he is talking about a little something called decorum.

 

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Advice for a reader: Is he that into me?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I recently received an email from a reader asking for advice. She doesn't want me to share her entire email with everyone so I am just going to give you the gist.

She recently met a guy from an online dating site and they have been spending time together. However she is a bit confused due to the fact that he's openly admitted that he is divorced, meets other chicks from the dating site, and is really hung up on woman he met a few months ago who currently has a boyfriend. So she wants to know if he is interested in her or just wants to be friends.

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Internet dating can be so complicated

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I received a message today on OkCupid. I am not positive if I would consider it an online dating message gone bad because it's definitely not the worst I have ever read. However, I am not really sure how I feel about it and it raised a few interesting thoughts/questions.

Here is the exact message I received:

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Does your boyfriend have to be friends with your friends?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Group of people relaxing around sofa, holding drinks and laughing

I've always been the girl who wanted a boyfriend who was friends with my friends. And I don't mean they play nice together when we are hanging out. No, I mean actual friends. You know the kind of friends who actually know things about one another. Maybe even hang out together when I am not around.

Call me totally crazy, but that is how I felt. My friends are important to me, always have been and always will be. In fact, I even consider my really close friends to be part of my family. So I guess it just seemed normal to want a guy to be a part of that. I can openly admit that I have had second thoughts about a guy who I thought might not "fit in" with my circle of friends.

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Could you date a guy who still lives with his parents?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Woman Dusting Houseplant

I love Sundays. Generally they are a pretty relaxing day for me. I drink a lot of coffee and write a lot. Sometimes I read and just try to relax. Actually, I am even known to cook a meal or two on Sundays. Another great thing is that Sundays are usually a great day for television, which is where I get to admit to watching some of the really lame shows that I actually watch.

I tend to be drawn to MTV occasionally on the weekends. There is often a marathon of shows like True Life or Made and what can I say, I am a fan of those shows for the most part. Hey it's a little better than my addiction to Teen Mom.

At any rate, earlier today I caught an episode of True Life which was about people who lived at home with their parents. I am pretty sure it's a fairly old episode of the show, but it's one that I hadn't watched before.

On the show there was a guy who was 30-something and still lived with his mom. He openly admitted to being a mama's boy and said he just hadn't had the desire to move out yet. He also openly admitted that he's never had a serious girlfriend and that he thinks it would be a little difficult to bring a lady friend home to his mom's house.

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In defense of the shy guy

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Man in boxers crouching

Recently I made a new friend. I kind of use the term friend loosely here as I have been engaging in a little flirtation with him. Read that as I have been flirting my ass off. He knows it and it seems to be pretty mutual.

Anyway, upon getting to know this guy, he has openly admitted to me on more than one occasion that he is a really shy guy - actually to be technical here he is a shy guy who is also on the clean cut side. This is generally the kind of guy that I have a really hard time meshing with and I know it's a problem for other women too.

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I'm a real man and I don't play games

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Side profile of a young couple playing scrabble

It seems like every time I am online looking through profiles on a dating site that I come across at least one guy that talks about how he doesn't play games or how he is looking for a girl that doesn't play games. This is something that I don't really understand.

First things first, some of these guys have a pretty awesome profile. I mean they talk about things they like to do and I feel like maybe this guy could be kind of interesting. But then, there it is "I am not looking for a woman who plays games" or "I am a real man. I don't play any games."

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Sometimes a guy comes back for more

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Screaming woman

Remember the guy from this post? Well he is back again. And as much as I would love to say that he turned out the be some really awesome guy, I am pretty sure I have to report that he is still the same. He sent me an IM the other day. At first I wasn't going to respond but he threw out an I'm sorry and I figured what the hell.

Now, let me just say here, that, yes, it does take more than an I'm sorry. But at the same time, I firmly believe that sometimes people are truly sorry and I genuinely want to believe in the good in (most) people. Plus, I mean technically I don't totally know this guy so I feel like it's important to give him the benefit of the doubt.

Well, I have learned my lesson with this guy. I mean really, I have truly learned my lesson.

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You have to pick up the phone once in a while

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Young Man with Cell Phone

A couple of days ago I read an awesome post over on the Queer Guy Tells It Straight. The post was about text dating, in other words people who use texting as their main form of communication while dating. I honestly couldn't agree more with his post and it made me want to throw my two cents in.

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A spade is a spade

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Senior man holding the ace of spades

A couple of nights ago, I had the opportunity to meet with the very talented blogger/writer Disaster on Heels. We had a pretty simple plan - flirt with some guys, celebrate National Singles Week, and of course enjoy the $2 beer special at the Kerryman. The night ended a little early when she realized she had lost her wallet which made her believe that she was living up to her name as a disaster (you can read more about that over on her blog).

She was more worried that she was coming across as that really bad date. You know the one where the person "forgets" their wallet so the other person has to pay. However, the bill was only a mere $20 so clearly that was not her plan. I was really just worried about her finding her wallet because I genuinely felt terrible for her. Plus, when the subject of my upcoming birthday came up she assumed I was turning 25, so I am pretty sure I would have forgiven her for anything after that.

At any rate, our quick lap around the bar to meet and mingle with some savvy single guys was pretty unsuccessful. We tried and I mean really tried but the only somewhat attractive guys were a group of three early 20 something's, one of whom was wearing a pink polo shirt. I wasn't even actually sure guys did that anymore and DOH mentioned you shouldn't do that after Labor Day. And she was a little distracted by the wallet situation. Can you blame her? That is one of my fears right there.

However, earlier in the evening, as we were about two beers in, we were chatting about the chaos (aka our internet dating lives) which obviously led to story swapping. I talked about a guy that I recently met and as I was telling the details I really started to think.

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Is too much hair a deal breaker?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I've never really been a woman that's into the hairy guy thing. In fact, when I was in college I was known to date plenty of guys that were hairless. Yes, I am talking no arm or leg hair (I actually did that a couple of times). It's kind of weird, I know. Actually my friends always told me it was really weird, but I just had this aversion to hair and I am really not sure why.

As I've grown a little older I have become far more tolerant. And while I really wouldn't say I am turned on by hair on a guy, I could really care less as long as it's not totally unruly and he still has great hygiene. Call me crazy, but I am a firm believer in upkeep. Plus I believe that fair is fair and if women have to go through all the annoyances to maintain, well then so do men.

Obviously I know how I feel, but I have always been curious about what other people think about this hairy situation and Jennifer Kelton from Bad Online Dates also became curious. So we made it our mission to find out.

To find out what Jennifer and I found out in both Los Angeles and Chicago head on over and read the full article on Bad Online Dates.

 

Are women too picky?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Couple shopping for jeans

I've been thinking a lot lately about this whole idea that women are too picky. It's not a big secret that people often think women dump men for silly things like wearing white socks with black pants or brown shoes with a black shirt and so on. I've known many women like that and I can admit that there was once a time that I found myself saying things like that when I realized I was losing interest in a guy.

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I'm depressed I don't have your number

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Invitation on a Slip of Paper

I have kind of neglected my OkCupid profile lately. It wasn't something that I did intentionally, it just really sort of happened. Though, I mean I feel like that seems pretty logical since I was busy planning my trip to New York and then I was actually In New York. Plus, we all know I have bad luck when I am busy and getting ready to go out of town.

Well, I came back and like any internet dating junkie I checked my messages. There wasn't really anything exciting there but while I was "online" I received two instant messages. One was from a fairly cute 22-year-old (the jury is still out on where I will go with that one) and the other was from a guy whom I have never met and haven't talked to in weeks for a few different reasons.

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If a woman says she's not interested that means she's not interested

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man Laughing

A little over a month ago, I talked about the guy who threatened that he was going out with other women because I was too busy to meet him. Well, he is back. Actually, to be quite technical he's made a few guest appearances here and there over the past month

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Sometimes I am busy (Part 2) - I don't respond to threats

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Man with laptop sitting on stool

Dating is frustrating (I am pretty sure I have said that before) and more often then not things don't go the way you want them to. Sometimes I think Saturday would be a great date night but the guy isn't available until Sunday. Sometimes I like guys that have no interest in me at all. And more often than I care to admit, I want what I can't have. We've all been there, but it's life and you have to deal with because let's face it there isn't really anything else to do about it.

I came back to the city earlier this week. Actually I came back a day later than I thought because there was a little mishap with the train schedule. Needless to say I was tired, a little cranky, and was really just ready to be home. Of course Mr. Doesn't Understand That I am busy that I talked about in my previous post started in with his spiel about how he really wants to meet me and so on.

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I would like a date that knows how to use grammar correctly

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I'm going to make a really huge and personal confession here. I am a grammar and spelling whore. Yes, I said it and it felt good and no I am not ashamed. Translation? It's a pretty necessary thing for any guy I date to know basic grammar and spelling. Now, this might seem like it's not that big of a deal or really all that hard to find but trust me it is. And anyone that has ever dated on the internet can vouch for me.

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I'm bored so do you want to go out?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Bored man waiting at table in restaurant

We've established that some guys need to learn what a date really is (and also a better place to meet women off the internet). Well, I kind of feel like we need to go into this whole asking a girl out on a date thing. I am just going to get straight to the point here, the words "I'm bored" should never be followed by "would you like to meet" (or any other derivative of that).

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Sitting on my couch is not a date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Destroyed couch

I've had a epiphany this week. Actually, back up for a second. Technically I have been thinking about this for a while, I just feel like it was fully confirmed this week. If you read my blog, you know that I am pretty open minded when it comes to dating and by no means am I a prissy princessy kind of girl. I have to be honest here though guys, sitting on my couch (or your couch) is not a date. Really, it's not.

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The 22-year-old approach to picking up an older woman

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Student Asleep During Lecture

Will someone please tell me what the deal is with 22-year-old guys? Seriously, their approach to picking up women (mainly older women) just flat out sucks.

Anyone who knows me will tell you that I am not overly fond of guys that are younger than I am (actually I am not overly fond of guys my age either). I tend to be into those that are more in the 32 to 35 age range - with an even bigger preference for those that are even older. Honestly I have no idea why this is; it's just how I have always been. Clearly I would love to say it's because I have better luck with older guys, but I am not really sure if I can say that.

Point being that there is a pretty big age difference between 22 and 32, especially in man years. So yes, I get that it's an age thing. Though, it's something that seems to be a trend which makes me wonder. And I mean, even if it is a 22-year-old is it too hard to ask for a little respect here?

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It's not giving up it's just moving on

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man sitting in back of van holding cup, low section

Anyone who knows me will tell you I am a pretty impatient person, I always have been. I am the type of person who likes to get things done and I always go after what I want. It's part of what brought me to the city - I need the hustle, the noise and all it's craziness. These are things that just seem natural to me, it's who I am. Sometimes I wonder, though, if it makes me give up too easily.

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Standards vs. rules in dating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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My friends sometimes think I am too open-minded; I often think they are crazy. I have always been a person who doesn't like to play by the rules, just ask my mother and my sister. It seems so easy to miss out on life when you are so busy worrying about the list of things you should be doing. Though, I have been noticing lately that this can be a problem with it comes to dating. And it's important to remember there is a huge difference between standards and rules.

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Using a crutch for sex is probably not your best laid plan

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man with crutch

We all have our staples when it comes to sex. A lot of women tend to have underwear or something that makes them feel sexy. Men sometimes do a couple of push ups when you are in the bathroom so they feel a little hotter. Those things I get. However, I have never in my life met a man that uses his apartment (or anything in it) as a crutch for sex.

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A cattle call won't ever get you the girl

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

2 cows in a pasture

Last night, I read a fabulous post over on The Queer Guy Tells It Straight. The post was about men trying to pick up women from their cars and how this attempt doesn't ever (and really definitely shouldn't ever) work.

I have to say that he is completely right here, fellas. In fact, I would say that, as a woman, I don't find anything even remotely flattering about a man who does this. If you are a woman who thinks this kind of behavior is flattering you seriously need to check your standards on how you feel a guy should treat you.

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Sometimes it's not a deal breaker, it's just down right picky

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

View of a young man picking out shirts from his wardrobe
The other day I was sitting on the bus on my way home from work and there was a girl next to me reading a magazine. I have no idea what magazine it was but there was a section about deal breakers in dating for women.
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Help! I'm on a disaster date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Couple yelling at each other

Shows on MTV are quite entertaining and since I was sick today, I caught a whole marathon of Disaster Date. In case you don't know, the idea behind the show is exactly what the title suggests. People hook their friends up on blind dates who do everything on their list of dating don'ts. The date and everyone else involved are all actors. Then the friends are given one dollar for every minute they stay on the date, the goal being for the date to last an hour.

 
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Please do not check out other women on a date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Anyone that knows me really well can tell you that there are certain things about my life that I am super anal about. For instance, I fold my towels all the same way and they are organized on the shelf by color. It's my system, always has been, and I don't like it when people mess with my system. When it comes to dating, however, I tend to be pretty laid back and open minded.

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Dating is a privilege not a right (part 2): You are not a princess

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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The other day, I read an awesome post from Single City Guy called Women Aren't Entitled to Anything which really made me think about how there are some women that feel they are entitled to certain behavior from men. You know, the whole idea that men should pay for everything, buy them gifts all the time, and generally worship the ground they walk on. I like to call this the princess behavior.
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Dating is a privilege not a right (part 1)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Let me start by saying that I am talking about both women and men here. You can call it my little disclaimer if you will, but I really feel this is a principle that applies to both sexes. Not that I am perfect (trust me I will be the first to name all my flaws if you ask me), but I personally feel pretty special when a guy I like wants to date me. So in return I like to try to show that as best I can.

When you first meet someone, they are generally pretty sweet and try to impress you, which generally continues at least through the first few dates. Sometimes, however, this nice thing stops and is replaced with the person's unwillingness to admit they like you. This generally happens because the person gets comfortable with the idea that you like them which then develops a cocky attitude. You know the whole idea that you like them so they can do no wrong.

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Five traits I never knew were deal breakers

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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A new book has surfaced which could make quite a few single women rethink their dating strategy. Marry Him: The Case for Settling for Mr. Good Enough by Lori Gottlieb hit store shelves yesterday and it's actually causing quite a controversy. The book is about exactly what the title suggests - women settling for "Mr. Good Enough" instead of holding out for "Mr. Perfectly Right."

I will admit that, as a single woman, I find the title of the book really hard to swallow. Honestly I think if I was a man I might have a few issues with it too. Since I haven't read the book I feel it's a little tacky and unfair to really critique it in anyway.

Though, my curiosity has been piqued, which of course led me to do a little research on the author and some of her ideas.

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Online dating messages gone bad: You look like a girl who is DTF

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Apparently there is a shirt that actually says it. This little shirt right here can be found at bufftees.com

Once again, I have yet another message to share from OkCupid to continue with my series Online Dating Messages Gone Bad.

This is actually a pretty short but not so very sweet message. As always I didn't change the message in anyway, just omitted any personal information. This is what was in my inbox:

Subject line: dtf

Message: you look like a girl who is dtf

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Should I keep seeing him?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I received an email the other day from a woman I know who is having a little dilemma with a guy she's recently started seeing. Here is the gist:

She met a guy through mutual friends and they immediately hit it off. A few days later they met for a quick drink and then that weekend they had their first "formal" date. Though he ended the date with a kiss she seems a little thrown by him. First, he asked her out via text, which is a huge no no in her book. Second, he didn't offer to pay for any of the date at all. Essentially she isn't sure if she should keep seeing him or not.

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The non-drinking guy: Deal breaker or not?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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One of my fellow bloggers Sex and the Windy City, brought up a really interesting point the other day when I wrote about drinking on the first date. She asked "what if you like to drink and your date is a non-drinker, is that a deal breaker?"

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Drinking on the first date (when your date isn't drinking)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Drunk Girl.jpg

When I wrote for examiner.com, one of my dating don'ts involved the subject of who should pay on a date. More specifically how you shouldn't be rude about paying for a date. Let's face it first date etiquette can be a little tricky especially when it comes to who should pay. It's an age old question and honestly I am not sure if there is a right or wrong answer, it's just something you have to deal with.

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Online dating messages gone bad: Hi hotty, I want be with you all day and night

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Continuing with my series called Online Dating Messages Gone Bad, I thought I would share this one.

The other day I was on OkCupid checking messages when I received an instant message. For those of you that don't know, OkCupid has its own instant messaging service so you can chat with other members. This is something I actually kind of like because it makes sending a message to a total stranger a little bit easier.

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Never trust a guy who never calls you over the weekend

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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It is my firm belief that if a guy only calls you on a Monday night that he's probably not worth your time. Now, I don't really mean Monday literally here, but more metaphorically. You know the guy that I am talking about. He calls you on Monday to see what you are doing and wants to do something that night, never making any sort of plans with you. Sometimes the calls continue through Tuesday or Wednesday but then they stop. Then all of a sudden he resurfaces as the next Monday rolls around.

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Deal breakers in dating: The bad first move

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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When you are dating guys over say the age of 25, it is inevitable that they have been on a date or two. Which also makes it pretty inevitable that they have kissed a girl and probably done all that sexual stuff too. Now, I am sure there is a 29-year-old out there somewhere that hasn't really been on a date with a woman. However, most of them have been around the block one or twice (some of them more times then they care to admit).

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A terrible advance won't get you into anyone's pants

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Last night, I had a phone conversation with a man that I had been chatting with on OKCupid. I have to say that I was slightly amused by the conversation, though I don't think it was the kind of amusement that most people are looking for to make a good first impression. Coincidentally, this is why I recommend a phone conversation or two before you actually meet in person. 

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